Short city breaks Province of Arezzo | Holiday Lettings UK

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  • Italy
  • Tuscany
  • Province of Arezzo
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  • Alberoro (2)
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  • Anghiari (19)
  • Arezzo (63)
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  • Bucine (13)
  • Caprese Michelangelo (3)
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  • Castel San Niccolo (2)
  • Castelfranco di Sopra (6)
  • Castelluccio, Arezzo (1)
  • Castelnuovo dei Sabbioni (1)
  • Castiglion Fibocchi (8)
  • Castiglion Fiorentino (18)
  • Cavriglia (8)
  • Chiusi della Verna (2)
  • Cicogna (1)
  • Civitella in Val di Chiana (7)
  • Cortona (116)
  • Creti (2)
  • Foiano Della Chiana (3)
  • Laterina (2)
  • Loro Ciuffenna (10)
  • Lucignano (16)
  • Monte San Savino (9)
  • Montegonzi (2)
  • Montevarchi (21)
  • Pergine Valdarno (20)
  • Pian di Sco (6)
  • Pieve Santo Stefano (3)
  • Poppi (10)
  • Pratovecchio (10)
  • Rigutino (2)
  • San Giovanni Valdarno (3)
  • San Giustino Valdarno (1)
  • San Pietro a Cegliolo (3)
  • Sansepolcro (11)
  • Sestino (1)
  • Stia (1)
  • Subbiano (7)
  • Talla (1)
  • Terranuova Bracciolini (9)
  • Tregozzano (1)
  • Val di Chiana (1)

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436 Holiday homes

Filters applied: City breaks (436)

(1) Excellent 

14

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £114 / night

£396 - £579 / week

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from £114 / night

(12) Excellent 

17

Borgo il Vepri - Ambra apartment sleeps 4

Province of Arezzo / Ambra

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Vepri is the perfect base for a tranquil holiday or home in the sun.It is for the discerning-a quiet and gated private luxury development comprising a small number of apartments and townhouses surrounding a communal piazza.The swimming pool is simply wonderful, set amid  …see more

from £43 / night

£295 - £479 / week

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from £43 / night

25

Province of Arezzo / Anghiari

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

 …see more

from £105 / night

£696 / week

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from £105 / night

28

Appartamento Giardino Centro - Lucignano apartment sleeps 4

Province of Arezzo / Lucignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Ask about pets
A fully self-contained apartment located in a medieval building opening onto its own garden, right in the centre of the charming central Tuscan town of Lucicnano.Appartamento Giardino is located in a a converted frantoio, olive oil mill is the centre of the medieval tow  …see more

from £73 / night

£461 - £651 / week

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from £73 / night

26

Cortona / Farinaio

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £87 / night

£783 - £1044 / week

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from £87 / night

(1) Excellent 

4

Villa Sonia, Cortona Tuscany - Cortona villa sleeps 6

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly
Villa Sonia is for sure, a really special property tucked away on the sleepy hillside of Cortona and, just a short distance form the enchanting franciscan monastery of Le Celle. Villa Sonia is perfect for four to 12 guests.This ancient stone farmhouse dates back to the  …see more

from £210 / night

£1470 - £1478 / week

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from £210 / night

35

Villa in the Chianti hills - Malva villa sleeps 14

Loro Ciuffenna / Malva

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
For those who love nature and the Tuscany countryside, our country villa “Oliveta” is the ideal holiday destination in Tuscany. The villa is located on the Aretine Chianti hills, in a lovely countryside area at the foot of Pratomagno mountain and along to the histor  …see more

from £127 / night

£957 - £1740 / week

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from £127 / night

(1) Excellent 

24

Province of Arezzo / Castiglion Fibocchi

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Pet friendly

 …see more

from £40 / night

£274 / week

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from £40 / night

18

Province of Arezzo / Cortona

11 20 1 night min

  • 11 bedrooms
  • Sleeps 20
  • 1 night min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

 …see more

from £522 / night

£3479 / week

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from £522 / night

(11) Excellent 

35

Villa Nobile is a stunning 19th Century Villa - Cortona villa sleeps 24

Province of Arezzo / Cortona

7 24 3 nights min

  • 7 bedrooms
  • Sleeps 24
  • 3 nights min
  • Nearest beach 250 km
  • Swimming pool
  • Child friendly
Villa Nobile is a stunning 19th Century classical style villa recently restored authentically and with artistic charm, with a private pool 13 m x 6 m. Sitting in 4 acres of natural Tuscan rural land. A private avenue of young cypresses bringing you to our doorstep. Tran  …see more

from £66 / night

£479 / week

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from £66 / night

16

Province of Arezzo / Badia Tedalda

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Nearest beach 85 km
  • Child friendly

 …see more

from £38 / night

£261 / week

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from £38 / night

(32) Excellent 

21

Tuscan Villa. Borgo Valecchie. Cortona - Montanare villa sleeps 10

Cortona / Montanare

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Nearest beach 180 km
  • Swimming pool
  • Child friendly
Our villa offers an ideal combination of elegant simplicity and historical charm which create a unique experience and can comfortably accommodate up to 10 guests. Located just five minutes away from The Hill town Cortona. Along with a private swimming pool, this holida  …see more

from £205 / night

£1435 - £2566 / week

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from £205 / night

37

Garibaldi, splendid apt in the centre Cortona - Cortona apartment sleeps 6

Province of Arezzo / Cortona

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
Garibaldi is a finely furnished and welcoming apartment, located on the first floor of a historic building having the same name of the Piazza that leads into the promenade in the centre of Cortona. The architecture of each area is enhanced by the choice of tones and fur  …see more

from £87 / night

£653 - £740 / week

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from £87 / night

(53) Excellent 

32

Villa Carda, luxury villa in Tuscany with private heated pool, jacuzzi, sauna and garden, sleeps up to 12 - Arezzo villa sleeps 12

Province of Arezzo / Arezzo

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Located on the hills that divide the Casentino valley from Chianti, the Villa is ideally positioned for those wishing to visit cities such as Florence, Arezzo or Siena.It is also the perfect base to experience and explore the Tuscan countryside.Now restored to perfectio  …see more

from £311 / night

£2174 - £4348 / week

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from £311 / night

(4) Excellent 

16

Province of Arezzo / Cavriglia

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 150 km
  • Child friendly
  • Air conditioning

 …see more

from £53 / night

£366 / week

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from £53 / night

(6) Excellent 

40

Casa Terrazza: Grand Tuscan house in medieval village with large terrace for alfresco dining, sleeps 7 - Lucignano house sleeps 7

Province of Arezzo / Lucignano

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
Casa Terrazza is located in Lucignano, one of the most outstanding examples of a fortified Tuscan mediaeval village. Casa Terrazza, is just a few steps away from restaurants and cafes.. Featuring a large terrace opening off main living area with views of the Val di Chi  …see more

from £130 / night

£853 - £1259 / week

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from £130 / night

28

Province of Arezzo / Castiglion Fibocchi

2 2 1 night min

  • 2 bedrooms
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £27 / night

£183 / week

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from £27 / night

(2) Excellent 

20

Province of Arezzo / Pian di Sco

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £44 / night

£287 - £409 / week

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from £44 / night

(2) Excellent 

21

Villa Cicaleta within walking distance to Cortona - Cortona farmhouse sleeps 7

Province of Arezzo / Cortona

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Swimming pool
Surrounded by olive groves and a 3000sqm private garden, the fenced-in holiday villa offers absolute peace and quiet at only 1,5 kilometres from the Etruscan Cortona, which can be easily reached on foot. The Trasimeno lake with its nice beaches and islands is at 8km and  …see more

from £150 / night

£1044 - £1305 / week

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from £150 / night

18

Rustic two bedroom Tuscan apartment close to Cortona's main square, wifi and parking available - Cortona apartment sleeps 2

Province of Arezzo / Cortona

2 2 1 night min

  • 2 bedrooms
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Ask owner if suitable for children
Quintani Sole - central apartmentApartment for 2 person and 1/2, compose by one bedroom + lounge with kitchen + 2 bathroom. WIFI, TV led, microwave, washing machine, toaster, kettle. Central position, near public parking and restaurants. Only 3 minute from main square a  …see more

from £70 / night

£435 / week

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from £70 / night

(2) Excellent 

10

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Private garden

 …see more

from £79 / night

£522 - £1066 / week

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from £79 / night

17

Province of Arezzo / Cortona

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Child friendly

 …see more

from £66 / night

£444 - £505 / week

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from £66 / night

(2) Excellent 

26

Province of Arezzo / Terranuova Bracciolini

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £261 / night

£1827 - £3653 / week

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from £261 / night

24

Villa Fonte - Cortona villa sleeps 12

Province of Arezzo / Cortona

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Villa Fonte is located in an extraordinary panoramic position in the open countryside surrounded by olive trees and other typical Tuscan plants but within walking distance from the famous historical town of Cortona just 400 meters away. The perfect place for a holiday d  …see more

from £417 / night

£2914 - £4522 / week

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from £417 / night

(17) Excellent 

24

Cortona / Montecchio, San Lorenzo

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £40 / night

£274 / week

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from £40 / night

(4) Very Good 

20

Province of Arezzo / Pratovecchio

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Pet friendly

 …see more

from £70 / night

£435 / week

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from £70 / night

20

Country House in Toscana - Pergine Valdarno - Pergine Valdarno farmhouse sleeps 8

Province of Arezzo / Pergine Valdarno

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
It's a countryhouse built in 19th century called "Podere La Vignaccia".The house, on two floors, has been recently restored and has all the comforts.At the groundfloor there's a double sitting room with a fireplace, a big kitchenroom with kitchenett  …see more

from £174 / night

£914 - £1400 / week

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from £174 / night

(4) Excellent 

29

Province of Arezzo / Anghiari

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets

 …see more

from £70 / night

£435 - £548 / week

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from £70 / night

(1) Excellent 

20

Province of Arezzo / Sestino

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £44 / night

£305 / week

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from £44 / night

(14) Very Good 

16

Arezzo / Capolona

4 20 3 nights min

  • 4 bedrooms
  • Sleeps 20
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £79 / night

£548 / week

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from £79 / night

(1) Excellent 

14

Province of Arezzo / Cortona

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £70 / night

£261 - £396 / week

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from £70 / night

25

IL GELSO - San Pietro a Cegliolo farmhouse sleeps 10

Province of Arezzo / San Pietro a Cegliolo

10 10 3 nights min

  • 10 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Sixteenth-century rural building, beautifully renovated in all its part, surrounded by greenery.It is located at the foot of the hill, where stands the ancient Etruscan town of Cortona. The farmhouse "Il Gelso" is equipped with swimming pool, and free secure p  …see more

from £27 / night

£183 - £1553 / week

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from £27 / night

(4) Excellent 

26

Arezzo / Capolona

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £87 / night

£522 - £827 / week

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from £87 / night

(9) Excellent 

18

Province of Arezzo / Cortona

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Suitable for children age 5+
  • Car not necessary

 …see more

from £61 / night

£400 - £435 / week

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from £61 / night

(1) Very Good 

15

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets

 …see more

from £87 / night

£522 - £696 / week

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from £87 / night

(1) Excellent 

26

Province of Arezzo / Arezzo

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £53 / night

£348 / week

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from £53 / night

8

Province of Arezzo / Arezzo

5 9 2 nights min

  • 5 bedrooms
  • Sleeps 9
  • 2 nights min
  • Child friendly
  • Pet friendly

 …see more

from £31 / night

£157 / week

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from £31 / night

(1) Excellent 

14

Luxury Tuscan Holiday Home , Stalla Rustica - Cortona house sleeps 8

Province of Arezzo / Cortona

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
An elegant, 17th Century Tuscan Farmhouse in a glorious location among Tuscan and Umbrian hills, only minutes from the beautiful Etruscan walled town of Cortona. Perfect all year round: walk or cycle in the hills, soak at the Thermal Spa, shop in fresh produce markets,  …see more

from £250 / night

£1495 / week

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from £250 / night

(3) Excellent 

24

Province of Arezzo / Sansepolcro

13 30 1 night min

  • 13 bedrooms
  • Sleeps 30
  • 1 night min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

 …see more

from £783 / night

£3914 / week

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from £783 / night

(34) Excellent 

35

Province of Arezzo / Poppi

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from £44 / night

£305 / week

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from £44 / night

Top Destination reviews

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A true TUSCAN experience. Better than words can describe.

It is quite a challenge to put into words a description of this place, the family and the amazing time we had at Vila Papale. The house and the entire property has so much history and character making this place a unforgettable experience. The garden … see more
Spacious and airy Volta Apartment - 2 bedrooms
Excellent apartment with friendly owner

We had a very warm welcome through Louise and her husband. What a wondeful flat, very spacious, lots of rooms and very much light through large windows. Louzise even purchased wine and some basic fod for the first days which was VERY generous and was … see more
Luxury villa with private swimming pool
AMAZING!!!

I've had the most wonderful stay in this Tuscan gem! Jacopo is such a great host and was always there to answer my questions. The villa is just beautiful! Each room and corner has something unique about it. The gardner Giancarlo came to make sure the … see more
Casa Dei Sogni, Tuscan Villa, Private Pool, A/C
Not to be missed

This Tuscan farmhouse has been tastefully and sympathetically restored. It is situated at the top of the valley with spectacular views of the surrounding countryside. You do need a car to stay here but most of the towns and villages to be explored … see more
To Stones
Amazing Home Away From Home

The best first impression was to be greeted late at night by Ester and her partner in the dark and in poor weather just so we could find a parking spot and get situated in the property. Ester was amazing and has gone to great lengths to ensure her ho … see more
Casa dei Sogni, Stefano - An attractive air conditioned stone farmhouse with Private Pool - set within a small Tuscan borgo
Not to be missed

This Tuscan farmhouse has been tastefully and sympathetically restored. It is situated at the top of the valley with spectacular views of the surrounding countryside. You do need a car to stay here but most of the towns and villages to be explored … see more

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